Water → HCID 131726183, compound

HRID 1372787Notes

Reaction equation

HRID 1372787 reaction equation
[CH3:1]I.[CH2:3]([O:10][C:11]([N:13]1[CH2:17][CH2:16][C@@H:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[C@:14]1([CH2:23][O:24][SiH:25]([CH3:27])[CH3:26])[OH:22])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H-].[Na+].O>CN(C=O)C>[CH2:3]([O:10][C:11]([N:13]1[CH2:17][CH2:16][C@@H:15]([C:18]([CH3:20])([CH3:21])[CH3:19])[C@:14]1([CH2:23][O:24][SiH:25]([CH3:27])[CH3:26])[O:22][CH3:1])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 131726184HCID 131726184, compound

Product 1

HCID 131726183HCID 131726183, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

In DMF (10 ml), methyl iodide (0.53 ml, 8.51 mmol) was added to N-benzyloxycarbonyl-(2R)-tert-butyldimethylsilyloxymethyl-(3S)-hydroxypyrrolidine (2.60 g, 7.11 mmol) and sodium hydride (0.34 g, 14.2 mmol) under stirring at 0° C. The reaction mixture was stirred further at the same temperature for 13 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (6:1, v/v) eluate fractions, N-benzyloxycarbonyl-(2R)-tert-butyldimethylsilyloxymethyl-(3S)-methoxypyrrolidine (2.73 g, 100%) as a colorless oil.

Workup

  1. stirringThe reaction mixture was stirred further at the same temperature for 13 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (6:1

Sources & evidence

ORD record
ord-2981b74a1a2843afb41c32d8e62d3bf2
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

Loading…